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WO1994009753A1 - Preparations cosmetiques deodorantes contenant des esters di- ou triglyceriques - Google Patents

Preparations cosmetiques deodorantes contenant des esters di- ou triglyceriques Download PDF

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Publication number
WO1994009753A1
WO1994009753A1 PCT/EP1993/002767 EP9302767W WO9409753A1 WO 1994009753 A1 WO1994009753 A1 WO 1994009753A1 EP 9302767 W EP9302767 W EP 9302767W WO 9409753 A1 WO9409753 A1 WO 9409753A1
Authority
WO
WIPO (PCT)
Prior art keywords
triglycerol
monocarboxylic acid
acid esters
deodorant
cosmetic
Prior art date
Application number
PCT/EP1993/002767
Other languages
German (de)
English (en)
Inventor
Helmut Dillenburg
Gerald Jakobson
Winfried Klein
Werner Siemanowski
Karlheinz Uhlig
Florian Wolf
Original Assignee
Beiersdorf Ag
Solvay Fluor Und Derivate Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Beiersdorf Ag, Solvay Fluor Und Derivate Gmbh filed Critical Beiersdorf Ag
Priority to DE59305359T priority Critical patent/DE59305359D1/de
Priority to US08/428,088 priority patent/US5648067A/en
Priority to JP51060794A priority patent/JP3650395B2/ja
Priority to EP93922925A priority patent/EP0666732B1/fr
Publication of WO1994009753A1 publication Critical patent/WO1994009753A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups

Definitions

  • the present invention relates to cosmetic deodorants.
  • Such formulations serve to eliminate body odor that arises when the odorless fresh sweat is decomposed by microorganisms.
  • the commercial cosmetic deodorants are based on different active principles.
  • antiperspirants the formation of sweat can be prevented by astringents - predominantly aluminum salts such as aluminum hydroxychloride (aluminum chlorohydrate).
  • astringents predominantly aluminum salts such as aluminum hydroxychloride (aluminum chlorohydrate).
  • aluminum hydroxychloride aluminum hydroxychloride
  • the substances used for this depending on their dosage, have a drastic effect on the heat balance of the armpit region and should only be used in exceptional cases.
  • the bacterial flora on the skin can be reduced.
  • only the odor-causing microorganisms should be effectively reduced. In practice, however, it has been found that the entire microflora of the skin can be affected.
  • the sweat flow itself is not affected by this, in the ideal case only the microbial decomposition of the sweat is temporarily stopped.
  • Perfuming cosmetic preparations containing active ingredients is not infrequently problematic because active ingredients and perfume components can occasionally react with one another and render one another ineffective.
  • Deodorants should meet the following conditions:
  • liquid deodorants for example aerosol sprays, roll-ons and the like, as well as solid preparations, for example deodorant sticks, powders, powder sprays, intimate cleansing agents, etc. are known and customary.
  • the object of the present invention was therefore to develop cosmetic deodorants which do not have the disadvantages of the prior art.
  • the deodorants should largely protect the microflora of the skin, but selectively reduce the number of microorganisms that are responsible for body odor.
  • a further task was to develop cosmetic deodorants which harmonize with the largest possible number of customary cosmetic auxiliaries and additives, in particular with the perfume constituents which are particularly important in formulations having a deodorant or antiperspirant effect.
  • a still further object of the invention was to provide cosmetic deodorants which are effective over a longer period of time, in the order of at least half a day, without their action noticeably diminishing.
  • fatty acid esters of glycerol ie monoglycerol
  • monoglycerol fatty acid esters in deodorising cosmetics, in particular glycerol onolaurate. Nevertheless, the effect of these monoglycerol esters lags far behind that of the monocarboxylic acid esters according to the invention.
  • the di- or triglycerol units of the monocarboxylic acid esters according to the invention are in the form of linear, unbranched molecules, ie "monoglycerol molecules” etherified via the respective OH groups in the 1- or 3-position.
  • a small proportion of cyclic di- or triglycerol units and glycerol molecules etherified via the OH groups in the 2-position can be tolerated. However, it is advantageous to keep such impurities as low as possible.
  • the monocarboxylic acid esters of diglycerol according to the invention are preferably monocarboxylic acid monoesters and are preferably characterized by the following structure (substitution positions indicated): 3 '2' 1 1
  • R 1 is a hydrocarbon, advantageously a branched or unbranched alkyl or alkenyl radical of 5 to 17 carbon atoms.
  • the monocarboxylic acid esters of triglycerin according to the invention are preferably monocarboxylic acid monoesters and are preferably characterized by the following structure (substitution positions indicated):
  • R " is a hydrocarbon, advantageously a branched or unbranched alkyl or alkenyl radical alkyl radical of 5 to 17 carbon atoms.
  • esters of diglycerol are preferred to those of triglycerol.
  • TML Triglycerol onolaurate
  • TMS Triglycerol Monomyristate
  • Diglycerol monocaprinate has proven to be the preferred monocarboxylic acid ester according to the invention.
  • the monofatty acid esters of diglycerol according to the invention are preferably in the 1-position, the monofatty acid esters of triglycerol according to the invention are preferably esterified in the 2'-position.
  • an additional proportion of di- or triglycerol esterified in other places is used, as is a proportion of the various diesters of di- or triglycerol where appropriate.
  • the diglycerol esters which are distinguished by two, and the triglycerol esters, which are characterized by three centers of asymmetry, are in all their configurations effective according to the invention.
  • the diglycerol esters have four, the triglycerol esters eight stereoisomers.
  • the 2-, the 2 'and the 2 "-positions are asymmetry centers.
  • mixtures of one or more monocarboxylic acid esters of diglycerol with one or more monocarboxylic acid esters of triglycerol are used.
  • the blends and / or substitute active ingredients are then advantageously present in a concentration of up to 50 parts by weight, preferably up to 35 parts by weight, based on the 100 parts by weight of the total amount resulting from the monocarboxylic acid ester or the monocarboxylic acid esters of diglycerol and / or triglycerol and these substitute active substances and / or extender compounds.
  • one or more monocarboxylic acid esters of diglycerol and / or one or more monocarboxylic acid esters of triglycerol are used in combination with other deodorizing or bacterial growth-inhibiting or bacteria-killing substances.
  • one or more monocarboxylic acid esters of diglycerol and / or one or more monocarboxylic acid esters of triglycerol are used in combination with monocarboxylic acid esters of glycerol (that is to say "monoglycerin").
  • monocarboxylic acid esters of glycerol take on the role of blending agents and / or substitute agents and are preferably used in a concentration of up to 50 parts by weight, preferably up to 35 parts by weight, based on 100 parts by weight of the total amount. which is composed of the monocarboxylic acid ester or the monocarboxylic acid esters of diglycerol and / or triglycerol and these monocarboxylic acid esters of glycerin.
  • R 1 is a hydrocarbon radical, advantageously a branched or unbranched alkyl or alkenyl radical of 5 to 17 carbon atoms.
  • the deodorizing effect of the esters according to the invention is based primarily on their selective toxicity for gram-positive, in particular coryneform, bacteria. These are considered to be the main germs responsible for the breakdown of apocrine sweat. Further the esters according to the invention are effective against staphylococci.
  • esters of the invention are also completely harmless to humans and other warm-blooded animals, they are ideally suited for use in cosmetic deodorants.
  • a method for controlling the human body odor caused by the microbial decomposition of apocrine sweat is further characterized in that an effective amount of monocarboxylic acid esters of di- and / or triglycerol, which may be present in a suitable cosmetic carrier, is applied to the skin.
  • monocarboxylic acid esters in particular monocarboxylic acid monoesters, of di- and / or triglycerol for combating gram-positive, in particular coryneform bacteria
  • monocarboxylic acid esters of di- and / or triglycerol to prevent the growth of gram-positive ones is also according to the invention. especially coryneform bacteria.
  • the cosmetic deodorants according to the invention are particularly advantageously characterized in that the monocarboxylic acid ester (s) of di- and / or triglycerol in concentrations of 0.01-10.00% by weight, preferably 0.05-5.00% by weight, particularly preferably 0.1-3.00% by weight, in each case based on the total weight of the composition, is or are present.
  • the cosmetic deodorants according to the invention can be in the form of aerosols, that is to say from aerosol containers, squeeze bottles or preparations sprayable by a pump device, or in the form of liquid compositions that can be applied by means of roll-on devices, as deodorant sticks (deodorant sticks ) and in the form of W / 0 or O / W emulsions that can be applied from normal bottles and containers, eg creams or lotions.
  • the cosmetic deodorants can advantageously be in the form of deodorising tinctures, deodorising intimate cleansing agents, deodorising shampoos, deodorising shower or bath preparations, deodorising powders or deodorising powder sprays.
  • ethanol and isopropanol, glycerol and propylene glycol, skin-caring fat or fat-like substances such as oleic acid decyl ester, cetyl alcohol, cetylstearyl alcohol and 2-0ctyldodecanol can be used as customary cosmetic carriers for the preparation of the deodorant preparations according to the invention in the quantitative ratios customary for such preparations as well as slime-forming substances and thickeners, e.g.
  • Hydroxyethyl or hydroxypropyl cellulose polyacrylic acid, polyvinylpyrrolidone, but also in small quantities cyclic silicone oils (polydimethylsiloxanes) and liquid polyphenylsiloxane low viscosity.
  • Suitable blowing agents for cosmetic deodorants according to the invention which can be sprayed from aerosol containers are the customary, known volatile, liquefied blowing agents, for example hydrocarbons (propane, butane, isobutane), which can be used alone or in a mixture with one another. Compressed air can also be used advantageously.
  • hydrocarbons propane, butane, isobutane
  • non-ionic types such as polyoxyethylene fatty alcohol ethers, e.g. Cetostearyl alcohol polyethylene glycol ether with 12 or 20 attached ethylene oxide units per molecule, cetostearyl alcohol and sorbitan esters and sorbitan ester ethylene oxide compounds (e.g. sorbitan monostearate and polyoxyethylene sorbitan onostearate) and long-chain, higher molecular weight wax-like polyglycol ethers proven to be suitable.
  • polyoxyethylene fatty alcohol ethers e.g. Cetostearyl alcohol polyethylene glycol ether with 12 or 20 attached ethylene oxide units per molecule
  • cetostearyl alcohol and sorbitan esters and sorbitan ester ethylene oxide compounds e.g. sorbitan monostearate and polyoxyethylene sorbitan onostearate
  • long-chain, higher molecular weight wax-like polyglycol ethers proven to be suitable.
  • BHT butylated hydroxytoluene
  • the pH of the formulations according to the invention is advantageously adjusted in the weakly acidic to weakly alkaline range, preferably from 4.0 to 9.0, particularly preferably from 5.0 to 6.5.
  • the amount of cosmetic carrier and perfume to be used in each case can easily be determined by a person skilled in the art depending on the type of product in question by simply trying it out.
  • the cosmetic preparations are prepared in a customary manner, usually by simply mixing with stirring, optionally with gentle heating. It has no difficulties.
  • fat phase and water phase e.g. prepared separately, if necessary with heating, and then emulsified.
  • the suspension bases for this can advantageously be selected from the group consisting of silica gels (for example those available under the trade name Aerosil), diatomaceous earth, talc, modified starch, titanium dioxide, silk powder, nylon powder, polyethylene powder and related substances.
  • the constituents mentioned under (a) are processed to a homogeneous solution, then slowly filled up with the water phase (b).
  • the finished pump spray can then be filled into pump atomizers.
  • the constituents mentioned under (a) are dispersed, water (c) is added, left to swell at room temperature, a solution of the constituents mentioned under (b) is added after about 15 minutes. The resulting mixture is homogenized and can be filled.
  • the ingredients are melted at approx. 75 ° C, mixed well and poured into suitable molds.
  • the constituents mentioned under (a) are processed to a homogeneous solution, then slowly filled up with the water phase (b).
  • the finished pump spray can then be filled into pump atomizers.
  • the constituents mentioned under (a) are dispersed, water (c) is added, left to swell at room temperature, a solution of the constituents mentioned under (b) is added after about 15 minutes. The resulting mixture is homogenized and can be filled.
  • the ingredients are melted at approx. 75 ° C, mixed well and poured into suitable molds.
  • the constituents mentioned under (a) are processed to a homogeneous solution, then slowly filled up with the water phase (b).
  • the finished pump spray can then be filled into pump atomizers.
  • the ingredients are melted at approx. 75 ° C, mixed well and poured into suitable molds.
  • Test organism Corynebacterium xerosis
  • Test substance 1 glycerol monolaurate (GML) (reference substance according to the prior art)
  • Test substance 2 diglycerol monocaprinate (DMC)
  • test substances were weighed out, mixed with 5 ml of AC medium and dissolved by heating to 60 ° C. for about 10 minutes.
  • the diagram shows the growth curves for the test approaches described above. Mean it

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)

Abstract

Déodorants cosmétiques caractérisés par une teneur efficace en esters d'acide monocarbonique de diglycérine et/ou triglycérine.
PCT/EP1993/002767 1992-11-03 1993-10-09 Preparations cosmetiques deodorantes contenant des esters di- ou triglyceriques WO1994009753A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DE59305359T DE59305359D1 (de) 1992-11-03 1993-10-09 Desodorierende kosmetische zubereitungen mit einem gehalt an di- oder triglycerinestern
US08/428,088 US5648067A (en) 1992-11-03 1993-10-09 Cosmetic deodorant preparation containing di- or triglycerin esters
JP51060794A JP3650395B2 (ja) 1992-11-03 1993-10-09 ある含量のジ−および／またはトリグリセロールのエステルを有する脱臭化粧配合物
EP93922925A EP0666732B1 (fr) 1992-11-03 1993-10-09 Preparations cosmetiques deodorantes contenant des esters di- ou triglyceriques

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4237081A DE4237081C2 (de) 1992-11-03 1992-11-03 Verwendung von Di- oder Triglycerinestern als Deowirkstoffe
DEP4237081.7 1992-11-03

Publications (1)

Publication Number Publication Date
WO1994009753A1 true WO1994009753A1 (fr) 1994-05-11

Family

ID=6471988

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1993/002767 WO1994009753A1 (fr) 1992-11-03 1993-10-09 Preparations cosmetiques deodorantes contenant des esters di- ou triglyceriques

Country Status (7)

Country Link
US (1) US5648067A (fr)
EP (1) EP0666732B1 (fr)
JP (1) JP3650395B2 (fr)
AT (1) ATE148338T1 (fr)
DE (2) DE4237081C2 (fr)
ES (1) ES2097546T3 (fr)
WO (1) WO1994009753A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995023586A3 (fr) * 1994-03-03 1995-09-28 Henkel Kgaa Compositions cosmetiques et/ou pharmaceutiques
WO1996003971A1 (fr) * 1994-07-30 1996-02-15 Beiersdorf Ag Preparations efficaces contre l'odeur des pieds, a teneur en esters oligoglyceriniques d'acides gras
EP1250842A1 (fr) * 2001-04-20 2002-10-23 Goldschmidt AG Composition pour combattre les microorganismes contenant une quantité efficace d'esters de polyglycerine
US7906664B2 (en) 2005-01-21 2011-03-15 Evonik Goldschmidt Gmbh Polyglycerol partial esters of polyricinoleic acid and polyfunctional carboxylic acids and the use thereof for producing emulsions and dispersions
US7910119B2 (en) 2005-03-11 2011-03-22 Evonik Goldschmidt Gmbh Cosmetic emulsions with long-term stability
EP1652431A3 (fr) * 2004-09-25 2012-02-08 Evonik Goldschmidt GmbH Agents à effet dépôt pour lutter contre les micro-organismes
WO2023025399A1 (fr) * 2021-08-27 2023-03-02 Symrise Ag Esters antimicrobiens pour le soin de la peau et du cuir chevelu

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EP1250842A1 (fr) * 2001-04-20 2002-10-23 Goldschmidt AG Composition pour combattre les microorganismes contenant une quantité efficace d'esters de polyglycerine
EP1652431A3 (fr) * 2004-09-25 2012-02-08 Evonik Goldschmidt GmbH Agents à effet dépôt pour lutter contre les micro-organismes
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US7910119B2 (en) 2005-03-11 2011-03-22 Evonik Goldschmidt Gmbh Cosmetic emulsions with long-term stability
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EP0666732B1 (fr) 1997-01-29
ATE148338T1 (de) 1997-02-15
DE4237081A1 (de) 1994-05-05
ES2097546T3 (es) 1997-04-01
JP3650395B2 (ja) 2005-05-18
DE4237081C2 (de) 1996-05-09
US5648067A (en) 1997-07-15
EP0666732A1 (fr) 1995-08-16
JPH08502500A (ja) 1996-03-19
DE59305359D1 (de) 1997-03-13

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